This is probably going to seem like one of the most big-headed questions you have been asked but I need your advice on finding a truly challenging job role.

I have applied to, and been employed in, far more jobs in my lifetime than can possibly be considered healthy. There is a common theme, if I am not initially overqualified I will always without fail come to terms with the job abnormally quickly. While in essence this seems like an advantage from the outside it is anything but; within a few weeks I will generally have mastered most aspects of the role, (assuming that the job contains no seasonal responsibilities,) in a few more weeks I start picking my duties apart in order to tailor them to my work style and within a few months I have the entire position down to a fine art. Which is where things get sticky, after this point I simply get bored and my motivation goes entirely downhill and I am either forced to take a new position or to exit the company entirely before my lack of focus begins affecting my performance.

This process has never taken longer than 6-7 months -often occurring even sooner- and as there are often no opportunities to move on to a more challenging position within the same company I end up leaving to find something else. While I have amassed several glowing recommendations in this fashion I’ve still never held a job consistently for longer than 8 months, and, it’s a cycle I can’t help but want to break.

Basically, I’m just asking what are the most challenging positions you have come across? (That don’t involve a start up. I’d rather save that rabbit hole for a few years down the line.)

I am a regular reader of your blog and a huge fan of your work.  I started following it in 2007. I was drawn to it because I was/am that classic twenty-something: lost.  I immediately found my post-undergrad job to be unsatisfying and boring.  I started in corporate finance.  I have since upgraded to an analyst position in asset valuation at a financial services firm.  I have been here three years and although I am not miserable, I daily yearn for something more.

I am in the process of researching NGO’s in Nepal.  I want to move there for 2-3 months to work in women’s empowerment.  I want to volunteer in Nepal because (a) I have spent the majority of the last five years making money for myself and my employers, not contributing much to humanity, (b) I want to immerse myself into a new culture and I find the Nepalese culture intriguing and (c) I want a hub to explore Asia (primarily after my commitment is fufilled in Nepal).  I have been to Asia twice and traveled throughout Europe in college so I am very confident in my traveling skills.

My biggest hesitation here has probably crossed your mind: what will I do upon my return?  I don’t know.  I am hoping that while abroad, I will be presented with new opportunities that will lead to my next step or, at the very least, my time overseas will shed some light on my next career move.  I am fairly certain that I do not want to stay in finance and I do not want to come back to Chicago, which is where I’ve lived for nearly five years.  One of my inclinations, among many, is to pursue a career in writing, using my material from a blog that I will keep while in Nepal and afterward.  My priorities of traveling and exploring will come second to writing my blog to ensure that I have a product when I return to the US (if I return).

What are your thoughts? Am I completely insane to pick up and leave (with approximately $10K in the bank) after building so much career equity in the past five years?  I am so lost and without a clear direction on my next “job” and I feel drawn to do something drastic and unconventional like this.

I went to art school and have been working in the creative industry for about five years now. I am going back to school this Fall for nursing though because I didn’t want to purely do art for the rest of my life. I see myself has having dual careers, nursing as the main one (day job) and art as the freelance one.

My question is about my LinkedIn profile!  Should I make my LinkedIn profile for nursing only? Art jobs boil down to the portfolio, so I think having a separate online presence will be enough for freelance. Yes, I think I answered my own question. I don’t think I should mix the two because it will confuse nurse recruiters.

I am in a serious dilemma in a crossroads in my life. My dad is an old school, wealthy conservative who wants me to join the workforce like he did and slave away my life to something I don’t necessarily feel good about. I can’t spend my life in a office, I simply can’t and I know this deep inside me.

My true passion lies in one thing- Poker. I have studied and played the game since I was 13 (I’m 22 now) and I have no doubt in my mind that it is what I want to do with my life. Don’t misjudge my passion though, it is not solely in pursuit of money. I have fallen in love with the game and the people. When I sit at a table and watch and study the people across from me I feel at home. I am competitive and intelligent, and I always have had a fascination with observing people and what drives them. I also love to meet people and be social. There is no better place to see every kind of person than at a poker table.

I want to watch people and guess what they are thinking every single day of my life. I want to die on the felt.

Here is the problem: I have one semester left in college and I had to pay for it on my credit card because my dad was not happy that I failed a class. I have always done well in school, but I find undergraduate school very pointless. I have learned nothing in college and I struggled to put any focus into it- I have always spent my time reading books about succeeding at poker. I am in debt and have no money to pursue what I want to and my dad won’t help me at it because he is severely against it.

Gambling has always been an iffy career choice, but the game, Texas Hold em, has stood the test of time and feeds many, many people as a career. My dad doesn’t believe me and won’t help me.

How do I get away from my debt and embark on my true passion?

– Anonymous Poker Player

I feel stuck.  I have been doing consulting in the Big 4 for around 10  years now and it’s just getting old.  I took the test and I am burnt out.  I took the other test and it appears that I may not have a good job and then I took another test and it shows me that I am an ISTJ. After you get the  result from that personality test it provides links to jobs that may be good for that type and I am already in those jobs and have been most of my 13 year career.

I feel like I have been trying to get out of consulting for years now, but now that I look at the openings that exist in my market that are outside of consulting, it appears that I don’t have the skills to do those and it feels  like consulting is the only thing I can do (which is not the case….I’ll admit to having a broader skill set than just being a consultant).  I don’t know where to start to get unstuck.  I need to reinvigorate my career and find interest in what I do or I need to find something else.

I am risk averse though.  My wife quit work 3 years ago to stay at home with our four kids.  We live comfortably on my salary, but I can’t take a massive pay cut to get into something that would potentially make me happier.  That will just lead to more stress.  Also, I am rooted firmly in Columbus.  All of my family is here and it’s a good place to raise a family.

I need to find something where I get some kind of fulfillment.  Telling  people all of the things they do wrong and how they could be better isn’t doing it for me lately.  I’m 36 and I feel like I hit a wall.  I am  unmotivated and constantly thinking about how can I get a new job that will provide something closer to an 8-5, will keep me off the road and will let me be more present in my kids lives.

My hope is that someone else has emailed you about this before and you can just copy and paste that answer here, but I know one size does not fit in with career advice.  I ordered a couple of the books you referenced on your site as well, so I am hoping that they provide some guidance or perspective.

Any insight you could provide would be much appreciated.

I’m in my mid-twenties and I’ve found that whenever I start a job, after a few days or so, I start feeling trapped and stuck.

I fear the regular routine of the job, being stuck in the 9-5 (or whatever my hours are) and being forced to work for the money versus doing something I love with a mission I care about. I’ve tried working for things that I believe are doing great things for the world (kid-focused startup and working with kids, which I’ve learned I’m not good at) and I still feel like that. Any kind of job with routine (even varying retail jobs and the like) scare me and thinking about applying to a job with more challenge in it (not getting that out of my current job) but that same routine worries me that I’ll be stuck there for a year or two working on building my skills for the better but still trapped inside a prison even if it is at a well-funded startup.

I’m an INFP programmer who loves logic and hopes to start my own startup someday as I get frustrated with not being able to make my own decisions. I’m not sure if I should go forward with my plan to find a job with that routine while I get great to build my skills for my own startup someday or if I should try to find something without that routine and if so, what? It doesn’t feel like most people have that same reaction to the stability of doing the same thing every day. About the only thing I know is I’m sick of not having money and I need to find something that allows me to have that. What should I do?

I am a 41-year-old single mom who needs to change the direction of her working life as a matter of mental survival. I’m a classic ENFJ kind of person and have been working behind a desk in isolation (I work in a suite of offices but the nature of our work is to remain quiet and alone) and it’s been wearing down my sanity.

I am absolutely in love with advertising and have always been but when I was young I didn’t choose to study it; it was too intimidating for me then. I’d love to be an ad account executive someday but getting started seems impossible from where I’m sitting. I’m reading everything I can get my hands on (marketing, too – it’s much drier but important to understand the basics) and bothering ad people for advice on how to get my foot in the door.

I have about two years to update my skills (before my daughter graduates from high school and I can focus on a career and/or live wherever I need) but very little money in which to make that happen. I can’t be a full-time unpaid intern; I have to pay bills and feed two people. I can be an evening and weekend person who is poorly paid, but with the abundance of free labor out there it’s tough.

I have a BS in Psychology, an MSW in Social Work and a strong background in writing and research. By nature I’m a collaborator, diplomat, convincer and intuitive, but those qualities can’t be put on a resume. I am not stubbornly stuck on working in advertising; something that is stimulating in a similar way would be wonderful, as long as it’s focused on people and ideas.

If you have any thoughts or advice for me I would very much appreciate either.

I work for a luxury apparel company – great group of people, but I’m not being creative and I feel like life is on repeat….sitting in an uncomfortable chair, staring at google and and eating my ritual salad. I am so not a ritual person.

I’ve had lots of life experiences, lots of jobs. I’m just trying to figure out what I’m passionate about and where I fit in in the job world. Do you have tips or models on how to narrow down your field of work you want to be in? I feel like I have so many things I enjoy and want to explore and its completely overwhelming at times. Well, all the time. I’ve done the pros and cons list over and over again. I just can’t nail it down. Any advice on how to nail it would be so great.

As a general rule of thumb, should people with ADD go on their own? I am trying hard at my third thing in three years and I am finding that I still make a lot of mistakes. It gets to a point where I space out and lose time. I try focusing and buckling down, but things still go bad.

A recent post on your blog talks about having challenging goals for which you can focus your energy on. You also mention you need to be able to make money doing it. Does that mean the only worthwhile goals that you focus on and try to reach everyday are ones that you can eventually make money from?